Abstract:

The present invention is an adamantane derivative which provides optical
characteristics such as transparency, (long term) light resistance and
the like, long term heat resistance, electric characteristics such as
dielectric constant and the like, and good mechanical properties; a
production method thereof; and a resin composition containing the
above-mentioned adamantane derivative that is an adamantane derivative
represented by general formulae (I) to (III); for example, a production
method of an adamantane derivative represented by the general formula
(III) by reacting an adamantane derivative represented by the general
formula (II) with acrylates, a resin composition containing an adamantane
derivative represented by the general formula (II) and an epoxy resin
curing agent, and a resin composition containing an adamantane derivative
represented by the general formula (III) and a thermopolymerization
initiator or a photopolymerization initiator.
In the formula, R1 represents CnH2n+1 (n is an integer of 1
to 10); R2 represents H, CH3, F or CF3; j is an integer of
1 to 4; k is an integer of 0 to 3; m is an integer of 2 to 5; and
j+k+m≦6.

Claims:

1. An adamantane derivative represented by the general formula (I),
##STR00011## [wherein R1 represents CnH2n+1 (n is an
integer of 1 to 10); j is an integer of 1 to 4; k is an integer of 0 to
3; m is an integer of 2 to 5; and j+k+m≦6.].

2. A method for producing an adamantane derivative represented by the
general formula (I), comprising reacting adamantane alcohols or
adamantane halides with phenols, ##STR00012## [wherein R1 represents
CnH2n+1 (n is an integer of 1 to 10); j is an integer of 1 to
4; k is an integer of 0 to 3; m is an integer of 2 to 5; and
j+k+m≦6.].

3. An adamantane derivative represented by the general formula (II),
##STR00013## [wherein R1 represents CnH2n+1 (n is an
integer of 1 to 10); j is an integer of 1 to 4; k is an integer of 0 to
3; m is an integer of 2 to 5; and j+k+m≦6.].

4. A method for producing an adamantane derivative represented by the
general formula (II), comprising reacting an adamantane derivative
represented by the general formula (I) with epichlorohydrin, ##STR00014##
[wherein R1 represents CnH2n+1 (n is an integer of 1 to
10); j is an integer of 1 to 4; k is an integer of 0 to 3; m is an
integer of 2 to 5; and j+k+m≦6.].

5. A resin composition containing an adamantane derivative represented by
the general formula (II) and an epoxy resin curing agent, ##STR00015##
[wherein R1 represents CnH2n+1 (n is an integer of 1 to
10); j is an integer of 1 to 4; k is an integer of 0 to 3; m is an
integer of 2 to 5; and j+k+m≦6.].

6. A cured product obtained by curing the resin composition according to
claim 5 by heating or light irradiation.

7. An adamantane derivative represented by the general formula (III),
##STR00016## [wherein R1 represents CnH2n+1 (n is an
integer of 1 to 10); R2 represents H, CH3, F, or CF3; j is
an integer of 1 to 4; k is an integer of 0 to 3; m is an integer of 2 to
5; and j+k+m≦6.].

8. A method for producing an adamantane derivative represented by the
general formula (III), comprising reacting an adamantane derivative
represented by the general formula (II) with acrylic acids, ##STR00017##
[wherein R1 represents CnH2n+1 (n is an integer of 1 to
10); R2 represents H, CH3, F, or CF3; j is an integer of 1
to 4; k is an integer of 0 to 3; m is an integer of 2 to 5; and
j+k+m≦6.].

9. A resin composition containing an adamantane derivative represented by
the general formula (III) and a thermopolymerization initiator or a
photopolymerization initiator. ##STR00018##

10. A cured product obtained by curing the resin composition according to
claim 9 by heating or light irradiation.

Description:

TECHNICAL FIELD

[0001]The present invention relates to a novel adamantane derivative
excellent in transparency, heat resistance and mechanical properties, a
production method thereof, and a resin composition containing the
adamantane derivative.

BACKGROUND ART

[0002]Adamantane is a highly symmetrical and stable compound in which four
cyclohexane rings are condensed to form a cage-like structure. The
derivative of adamantane is known as a useful raw material for
pharmaceuticals, highly functional industrial materials and the like
because of its unique functions. For example, attempts to use the
adamantane derivative for a substrate of an optical disk, an optical
fiber, a lens, and the like are being made because the adamantane
derivative has optical characteristics, heat resistance, and the like
(for example, refer to Patent Documents 1 and 2). Further, attempts to
use adamantane esters as a raw material for a photoresist resin are also
being made by employing its acid sensitivity, resistance to dry etching,
transmittance of an ultraviolet light, and the like (for example, refer
to Patent Document 3).

[0003]In recent years, in the field of electronic and optical materials,
investigation is progressing to enhance or improve the performance of
optical and electronic parts. Examples of such investigation are
improvement of fineness, widening of view angle, and improvement of image
quality of a flat panel display using liquid crystal, organic
electroluminescence (organic EL) and the like, increasing of brightness,
shortening of wavelength, and increasing of whiteness of the light source
using an optical semiconductor such as a light-emitting diode (LED) and
the like, as well as increasing of frequency of electronic circuit and
optical circuit and optical communication. In addition, semiconductor
technology is significantly progressing and electronic devices are
rapidly becoming miniaturized, light-weighted, highly performed, and
multifunctionalized. In response to this trend, high density and multiple
wiring are desired for interconnection substrates.

[0004]On the other hand, epoxyacrylate resins are used for various coating
agents, structural materials, a solder resist for an interconnection
substrate, a protection film for a color filter of a liquid crystal
display and an image sensor, a color resist, and the like. As for a
solder resist, a bisphenol-A type epoxyacrylate resin is disclosed (for
example, refer to Patent Document 4). As for a photosensitive composition
for a color filter, a cresol-novolac type epoxyacrylate resin is
disclosed (for example, refer to Patent Document 5). However, the
transparency, (long-term) heat resistance, and (long-term) light
resistance of these epoxyacrylate resins are limited and materials
satisfying those demanded characteristics are desired.

[0005]In the epoxy resins, thermosetting-type resins such as conventional
bisphenol-A type epoxy resins and the like have the same problems as
mentioned above and sealing materials satisfying those demanded
characteristics are also desired (for example, refer to Non-patent
Document 1).

[0006]In addition, as for the electronic circuit integrated with
semiconductors and the like, in association with the progress of
information-oriented society, information quantity and communication
speed are increasing and the apparatuses are being miniaturized.
Therefore, the miniaturization, integration, and increasing of frequency
of the circuit are required. Furthermore, an optical circuit using an
optical waveguide and the like which enables more rapid processing is
also investigated. For these applications, bisphenol-A type epoxy resins,
epoxyacrylate resins, and the like are conventionally used as a sealing
resin, an adhesive resin or film, or a resin for lens. However, there are
problems of high dielectric constant, poor heat resistance and the like
in using these resins in the electronic circuit. In the optical waveguide
and sealing of LED, there are problems of decreased transparency,
yellowing of the resin by degradation, and the like.

[0013]From the circumstances mentioned above, an object of the present
invention is to provide an adamantane derivative suitable as a solder
resist for an interconnection substrate, a protection film for a color
filter of a liquid crystal display and a solid-state imaging element, a
colored composition for a color filter, interlayer insulation film for a
liquid crystal display, a sealant for an electronic circuit (a sealant
for an optical semiconductor and a sealant for an organic EL element), an
optoelectronic part (an optical waveguide, a lens for optical
communication, an optical film, and the like), and adhesives for these
devices, and others, and having optical characteristics such as
transparency, (long-term) light resistance, and the like, long-term heat
resistance, electric characteristics such as dielectric constant and the
like, and good mechanical properties; a production method of the
adamantane derivative; and a resin composition containing the
above-mentioned adamantane derivative.

[0014]As a result of keen examination, the present inventors found that a
resin composition which provides a cured product suitable as an
optoelectronic part and the like is obtained from an adamantane
derivative having a specific structure. The present invention has been
completed based on this finding.

[0015]Thus, the present invention provides an adamantane derivative
mentioned below, a production method thereof, and a resin composition
containing the adamantane derivative. [0016]1. An adamantane derivative
represented by the general formula (I),

##STR00001##

[0016][wherein R1 represents CnH2n+1 (n is an integer of 1
to 10); j is an integer of 1 to 4; k is an integer of 0 to 3; m is an
integer of 2 to 5; and j+k+m≦6.]. [0017]2. A method for producing
an adamantane derivative represented by the general formula (I),
comprising reacting adamantane alcohols or adamantane halides with
phenols,

##STR00002##

[0017][wherein R1, j, k, and m are the same as above.]. [0018]3. An
adamantane derivative represented by the general formula (II),

##STR00003##

[0018][wherein R1, j, k, and m are the same as above.]. [0019]4. A
method for producing an adamantane derivative represented by the general
formula (II), comprising reacting an adamantane derivative represented by
the general formula (I) with epichlorohydrin,

##STR00004##

[0019][wherein R1, j, k, and m are the same as above.]. [0020]5. A
resin composition containing an adamantane derivative represented by the
general formula (II) and an epoxy resin curing agent,

##STR00005##

[0020][wherein R1, j, k, and m are the same as above.]. [0021]6. A
cured product obtained by curing the resin composition described in the
above-mentioned 5 by heating or light irradiation. [0022]7. An adamantane
derivative represented by the general formula (III),

##STR00006##

[0022][wherein R1, j, k, and m are the same as above; and R2
represents H, CH3, F, or CF3.]. [0023]8. A method for producing
an adamantane derivative represented by the general formula (III),
comprising reacting an adamantane derivative represented by the general
formula (II) with acrylic acids,

##STR00007##

[0023][wherein R1, R2, j, k, and m are the same as above.].
[0024]9. A resin composition containing an adamantane derivative
represented by the general formula (III) and a thermopolymerization
initiator or a photopolymerization initiator,

##STR00008##

[0024][wherein R1, R2, j, k, and m are the same as above.].
[0025]10. A cured product obtained by curing the resin composition
described in the above-mentioned 9 by heating or light irradiation.

[0026]The adamantane derivative of the present invention provides a cured
product suitable as a solder resist for an interconnection substrate, a
protection film for a color filter of a liquid crystal display and an
image sensor, a colored composition for a color filter, a sealant for an
electronic circuit (a sealant for an optical semiconductor and a sealant
for an organic EL element), an optoelectronic part (an optical waveguide,
a lens for optical communication, an optical film, and the like), and
adhesives for these devices, and others, and excellent in optical
characteristics such as transparency, (long-term) light resistance, and
the like, (long-term) heat resistance, and mechanical properties.

BEST MODE FOR CARRYING OUT THE INVENTION

[0027]The adamantane derivative of the present invention is a phenolic
hydroxyl group-containing adamantane derivative represented by the
following general formula (I), a glycidyloxy group-containing adamantane
derivative represented by the following general formula (II), and an
adamantyl group-containing epoxy modified acrylates represented by the
following general formula (III).

##STR00009##

(In the formula, R1 represents CnH2n+1 (n is an integer of
1 to 10, preferably 1 to 5); R2 represents H, CH3, F, or
CF3; j is an integer of 1 to 4, preferably 1 to 3; k is an integer
of 0 to 3, preferably 0 to 2; m is an integer of 2 to 5, preferably 2 or
3; and j+k+m≦6.)

[0028]In the above-mentioned general formulae (I) to (III), examples of
R1 include a methyl group, an ethyl group, an n-propyl group, an
iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl
group, a t-butyl group, various pentyl groups, various hexyl groups,
various octyl group, and the like. When there are plural R1s, they
may be the same or different from each other. In the above-mentioned
general formula (III), examples of the group containing R2 include a
(2-acryloyloxy-2-hydroxy)ethoxy group, a
(2-methacryloyloxy-2-hydroxy)ethoxy group, a
(2-α-fluoroacryloyloxy-2-hydroxy)ethoxy group, and a
(2-α-trifluoromethylacryloyloxy-2-hydroxy)ethoxy group. When j is 2
to 4 in the above-mentioned general formula (III), they may be the same
or different from each other.

[0029]The phenolic hydroxyl group-containing adamantane derivative
represented by the above-mentioned general formula (I) can be obtained by
reacting adamantane alcohols or adamantane halides with phenols.

[0031]The amount of these adamantane alcohols or adamantane halides to be
used is usually approximately 2 to 20 moles, preferably 2 to 10 moles,
per mole of the phenols. When the amount to be used is 2 moles or more
per mole of the phenols, the reaction time is not too long and adequate.

[0033]The reaction of adamantane alcohols or adamantane halides and
phenols is usually carried out in the presence of an acid catalyst.
Examples of the acid catalyst include hydrochloric acid, sulfuric acid,
p-toluenesulfonic acid, thioacetic acid, β-mercaptopropionic acid
and the like. The amount of this acid catalyst to be used is usually
approximately 0.01 to 1 mole, preferably 0.05 to 0.8 mole per mole of the
functional group of the adamantane alcohols or adamantane halides as a
raw material. When the amount of the acid catalyst to be used is 0.01
mole or more per mole of the functional group, the reaction time is not
too long and adequate. When the amount of the acid catalyst to be used is
1 mole or less per mole of the functional group, the balance of the
attained effect and economic efficiency is good.

[0034]In the reaction, a solvent may be used as needed. Specific examples
of the solvent include cyclohexane, heptane, octane, decane, toluene, DMF
(dimethylformamide), DMAc (N,N-dimethylacetamide), DMSO
(dimethylsulfoxide), ethyl acetate, diethyl ether, tetrahydrofuran,
dimethoxyethane, methanol, ethanol, isopropyl alcohol, acetic acid,
propionic acid and the like. These solvents may be used alone or in
combination of two or more kinds.

[0035]The reaction of the adamantane alcohols or adamantane halides and
phenols is usually carried out at a temperature of approximately 0 to
200° C., preferably 50 to 150° C. When the reaction
temperature is 0° C. or higher, the reaction rate is not lowered
and adequate, therefore the reaction time is shortened. When the reaction
temperature is 200° C. or lower, discoloration of the product is
suppressed. The reaction pressure is approximately 0.01 to 10 MPa,
preferably normal pressure to 1 MPa, in absolute pressure. When the
pressure is 10 MPa or less, the safety is secured and special equipment
is not required, therefore this method is industrially useful. The
reaction time is usually approximately 1 minute to 24 hours, desirably 1
to 10 hours.

[0045]The glycidyloxy group-containing adamantane derivative represented
by the above-mentioned general formula (II) can be obtained by reacting
the phenolic hydroxyl group-containing adamantane derivative represented
by the above-mentioned general formula (I) with epichlorohydrin. In the
reaction with epichlorohydrin, the above-mentioned phenolic hydroxyl
group-containing adamantane derivative may be used alone or in a mixture
of two or more kinds.

[0047]The ratio of the basic catalyst to be used to the phenolic hydroxyl
group-containing adamantane derivative represented by the general formula
(I) as a raw material for the reaction is selected so that the molar
ratio of the basic catalyst to the active hydrogen of the monomer as a
raw material is approximately 0.8 to 10, preferably 1 to 5.

[0048]In the above-mentioned reaction, a quarternary ammonium salt such as
tetramethylammonium chloride, tetraethylammonium chloride,
tetraethylammonium bromide and the like may be added as a phase transfer
catalyst. The ratio of the quarternary ammonium salt to be used is
approximately 0.01 to 20 mol %, preferably 0.1 to 10 mol % to the
phenolic hydroxyl group-containing adamantane derivative.

[0049]The reaction is carried out in the absence or in the presence of a
solvent. The solvent is advantageously selected so that the solubility of
the above-mentioned phenolic hydroxyl group-containing adamantane
derivative is 0.5 mass % or more, desirably 5 mass % or more. The amount
of the solvent to be used is selected so that the concentration of the
above-mentioned phenolic hydroxyl group-containing adamantane derivative
is 0.5 mass % or more, desirably 5 mass % or more. In this reaction,
although the above-mentioned phenolic hydroxyl group-containing
adamantane derivative may be reacted in a suspended state, it is
desirable that the derivative is dissolved in the solvent. Specific
examples of the solvent include hexane, heptane, toluene, DMF
(dimethylformamide), DMAc (N,N-dimethylacetamide), DMSO
(dimethylsulfoxide), ethyl acetate, diethyl ether, THF (tetrahydrofuran),
acetone, methyl ethyl ketone, MIBK (methyl isobutyl ketone) and the like.
These solvents may be used alone or in combination of two or more kinds.

[0050]The reaction of the phenolic hydroxyl group-containing adamantane
derivative and epichlorohydrin is usually carried out at a temperature of
approximately 0 to 200° C., preferably 20 to 150° C. When
the reaction temperature is 0° C. or higher, the reaction rate is
not lowered and adequate, therefore the reaction time is shortened. When
the reaction temperature is 200° C. or lower, discoloration of the
product is suppressed. The reaction pressure is approximately 0.01 to 10
MPa, preferably normal pressure to 1 MPa, in absolute pressure. When the
pressure is 10 MPa or less, the safety is secured and special equipment
is not required, therefore this method is industrially useful. The
reaction time is usually approximately 1 minute to 24 hours, desirably 1
to 10 hours.

[0051]Usually, a compound containing a group having an epoxy ring contains
an oligomer component of dimer or multimer. Therefore, in the
above-mentioned reaction, an oligomer, that is, a dimer or multimer, of
the glycidyloxy group-containing adamantane derivative is formed.
Although the presence of these oligomers does not cause any problem, the
product is purified by distillation, crystallization, column separation,
and the like, as needed. The method of purification may be selected
according to the characteristics of the reaction product and the kind of
the impurities.

[0052]In the above-mentioned reaction, when the production of the
glycidyloxy group in the glycidyloxy group-containing adamantane
derivative is not sufficient, the amount of the glycidyloxy group may be
improved by a ring closing reaction using a basic catalyst.

[0053]This ring closing reaction is usually carried out at a temperature
of approximately 20 to 200° C., desirably 30 to 150° C. The
reaction pressure is approximately 0.01 to 10 MPa, desirably normal
pressure to 1 MPa, in absolute pressure. When the pressure is 10 MPa or
less, the safety is secured and special equipment is not required,
therefore this reaction is industrially useful. The reaction time is
usually approximately 1 minute to 24 hours, desirably 30 minutes to 10
hours.

[0055]The amount of the basic catalyst to be used is approximately 0.1 to
20 mass %, preferably 1 to 10 mass %, relative to the glycidyloxy
group-containing adamantane derivative represented by the above-mentioned
general formula (II). When the amount of the basic catalyst to be used is
0.1 mass % or more, the reaction rate is not lowered and adequate,
therefore the reaction time is shortened. When the amount of the basic
catalyst to be used is 20 mass % or less, the balance of the attained
effect and economic efficiency is good.

[0056]The reaction may be carried out in the absence or in the presence of
a solvent. The solvent is advantageously selected so that the solubility
of the glycidyloxy group-containing adamantane derivative represented by
the general formula (II) is 0.5 mass % or more, desirably 5 mass % or
more. The amount of the solvent to be used is selected so that the
concentration of the above-mentioned glycidyloxy group-containing
adamantane derivative is 0.5 mass % or more, desirably 5 mass % or more.
In this reaction, although the above-mentioned glycidyloxy
group-containing adamantane derivative may be reacted in a suspended
state, it is desirable that the derivative is dissolved in the solvent.
Specific examples of the solvent include hexane, heptane, toluene, DMF
(dimethylformamide), DMAc (N,N-dimethylacetamide), DMSO
(dimethylsulfoxide), ethyl acetate, diethyl ether, tetrahydrofuran,
acetone, MEK (methyl ethyl ketone), MIBK (methyl isobutyl ketone) and the
like. These solvents may be used alone or in combination of two or more
kinds.

[0057]The reaction product is purified by distillation, crystallization,
column separation, and the like. The method of purification may be
selected according to the characteristics of the reaction product and the
kind of the impurities.

[0067]The adamantyl group-containing epoxy modified acrylates represented
by the above-mentioned general formula (III) can be obtained by reacting
the glycidyloxy group-containing adamantane derivative represented by the
above-mentioned general formula (II) with acrylic acids. In this
acrylation reaction, the above-mentioned glycidyloxy group-containing
adamantane derivative may be used alone or in a mixture of two or more
kinds.

[0068]Examples of the acrylic acids used include acrylic acid, methacrylic
acid, α-fluoroacrylic acid, and α-trifluoromethylacrylic
acid. These acrylic acids may be used alone or in a mixture of two or
more kinds.

[0069]The reaction between the above-mentioned glycidyloxy
group-containing adamantane derivative and acrylic acids is usually
carried out in the presence of a catalyst. Examples of the catalyst used
include an organic amine such as triethylamine, tributylamine, pyridine,
dimethylaminopyridine and the like; a quarternary ammonium salt such as
tetramethylammonium chloride, tetramethylammonium bromide,
tetraethylammonium chloride, tetraethylammonium bromide and the like;
triphenylphosphine; and others. The amount of the catalyst to be used is
usually approximately 0.01 to 20 mass %, preferably 0.05 to 15 mass %,
relative to the acrylic acids.

[0070]The reaction is carried out in the absence or in the presence of a
solvent. The solvent is advantageously selected so that the solubility of
the above-mentioned glycidyloxy group-containing adamantane derivative is
0.5 mass % or more, desirably 5 mass % or more. In this reaction,
although the above-mentioned glycidyloxy group-containing adamantane
derivative may be reacted in a suspended state, it is desirable that the
derivative is dissolved in the solvent. Specific examples of the solvent
include cyclohexane, methylcyclohexane, ethylcyclohexane, toluene,
xylene, MEK, MIBK (methyl isobutyl ketone), DMF (dimethylformamide), NMP
(N-methyl-2-pyrrolidone), DMAc (N,N-dimethylacetamide), DMSO
(dimethylsulfoxide), propyleneglycol monomethyl ether acetate and the
like. These solvents may be used alone or in combination of two or more
kinds.

[0071]The reaction of the glycidyloxy group-containing adamantane
derivative and acrylic acids is usually carried out at a temperature of
approximately 50 to 200° C., preferably 70 to 150° C. When
the reaction temperature is 50° C. or higher, the reaction rate is
not lowered and adequate, therefore, the reaction time is shortened. When
the reaction temperature is 200° C. or lower, side reaction is
suppressed and discoloration of the product is suppressed. The reaction
pressure is approximately 0.01 to 10 MPa, desirably normal pressure to 1
MPa in absolute pressure. When the pressure is 10 MPa or less, the safety
is secured and special equipment is not required, therefore this method
is industrially useful. The reaction time is usually approximately 1
minute to 24 hours, desirably 1 to 10 hours.

[0072]In the reaction, a polymerization inhibitor such as hydroquinone,
methoquinone, phenothiazine, methoxyphenothiazine and the like may be
added as needed. The ratio of the polymerization inhibitor to be used is
usually approximately 10 to 10,000 mass ppm, preferably 50 to 5,000 mass
ppm, to the acrylic acids.

[0073]The reaction product is purified by distillation, crystallization,
column separation, and the like. The method of purification may be
selected according to the characteristics of the reaction product and the
kind of the impurities.

[0074]Examples of the adamantyl group-containing epoxy modified acrylates
represented by the above-mentioned general formula (III) thus obtained
may include the compounds as exemplified by the glycidyloxy
group-containing admantane derivative represented by the above-mentioned
general formula (II) in which "glycidyloxybenezene" is replaced by
"-[(2-acryloyloxy-2-hydroxy)ethoxy]benzene",
"-[(2-methacryloyloxy-2-hydroxy)ethoxy]benzene",
"-[(2-α-fluoroacryloyloxy-2-hydroxy)ethoxy]benzene", and
"-[(2-α-trifluoromethylacryloyloxy-2-hydroxy)ethoxy]benzene".

[0075]The resin composition (1) of the present invention contains the
glycidyloxy group-containing adamantane derivative represented by the
above-mentioned general formula (II) and an epoxy resin curing agent. In
the resin composition (1) of the present invention, a mixture of the
glycidyloxy group-containing adamantane derivative represented by the
above-mentioned general formula (II) and other known epoxy resins may
also be used in order to optimize the mechanical strength of the cured
product and the solubility, workability, and the like of the resin
composition.

[0077]The above-mentioned known epoxy resins may be either solid or liquid
at ordinary temperature, but in general, it is preferable that the
average epoxy equivalent of the epoxy resin to be used is 100 to 2,000.
When the epoxy equivalent is 100 or more, the cured product of the
composition of the present invention does not become brittle and an
adequate strength is obtained. In addition, when the epoxy equivalent is
2,000 or less, the glass transition temperature (Tg) of the cured product
does not become lower and an adequate Tg is obtained.

[0078]The content of the above-mentioned glycidyloxy group-containing
adamantane derivative in the mixture of the above-mentioned glycidyloxy
group-containing adamantane derivative and the above-mentioned known
epoxy resin is preferably 5 mass % or more, more preferably 10 mass % or
more. When the content of the glycidyloxy group-containing adamantane
derivative is 5 mass % or more, the optical characteristics, long-term
heat resistance, and electric characteristics of the resin composition of
the present invention are sufficient.

[0079]As an epoxy resin curing agent contained in the resin composition
(1) of the present invention, at least one kind selected from a cationic
polymerization initiator, an acid anhydride curing agent, an amine curing
agent, a phenolic curing agent, and the like is mentioned. That is, the
resin composition (1) of the present invention is cured by a reaction
using such an epoxy resin curing agent.

[0080]As the cationic polymerization initiator, one which reacts with an
epoxy ring by heat or an ultraviolet light may be used. The examples
include an aromatic diazonium salt such as p-methoxybenzenediazonium
hexafluorophosphate and the like, an aromatic sulfonium salt such as
triphenylsulfonium hexaflurophosphate and the like, an aromatic iodonium
salt such as diphenyliodonium hexafluorophosphate and the like, an
aromatic iodosyl salt, an aromatic sulfoxionium salt, metallocene
compound and the like. Among these, an aromatic sulfonium salt such as
triphenylsulfonium hexafluorophosphate and the like and an aromatic
iodonium salt such as diphenyliodonium hexafluorophosphate and the like
are most suitable. These initiators may be used alone or in combination
of two or more kinds.

[0081]The amount of the cationic polymerization initiator to be used is
preferably 0.01 to 5.0 parts by mass, more preferably 0.1 to 3.0 parts by
mass, relative to 100 parts by mass of the above-mentioned glycidyloxy
group-containing adamantane derivative or the above-mentioned mixed resin
(hereinafter, optionally referred to as "resin component"). By setting
the content of the cationic initiator in the above-mentioned range, good
polymerization characteristics and physical properties such as optical
characteristics and the like can be expressed.

[0082]Examples of the acid anhydride curing agent include phthalic
anhydride, maleic anhydride, trimellitic anhydride, pyromellitic
anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride,
methylnadic anhydride, nadic anhydride, glutaric anhydride,
methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride and
the like. Among these, hexahydrophthalic anhydride, tetrahydrophthalic
anhydride, methylhexahydrophthalic anhydride, and
methyltetrahydrophthalic anhydride are most suitable. These anhydrides
may be used alone or in combination of two or more kinds.

[0083]When the acid anhydride curing agent is used, a curing accelerator
may be blended in order to accelerate the curing. Examples of the curing
accelerator include tertiary amines, imidazoles, organic phosphine
compounds, or salts of them, and metal soaps such as zinc octylate, tin
octylate and the like. These curing accelerators may be used alone or in
combination of two or more kinds.

[0084]Examples of the phenolic curing agent include phenol novolac resin,
cresol novolac resin, bisphenol-A novolac resin, triazine modified phenol
novolac resin and the like. Examples of the amine curing agent include
dicyandiamide; aromatic diamine such as m-phenylenediamine,
4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone,
m-xylylenediamine and the like; and others. These curing agents may be
used alone or in combination of two or more kinds.

[0085]Among these curing agents, acid anhydride curing agents are suitable
from a viewpoint of a physical property such as transparency and the like
of the cured resin. Among these, hexahydrophthalic anhydride,
tetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, and
methyltetrahydrophthalic anhydride are most suitable.

[0086]The ratio of the resin component and the curing agent is determined
by the ratio of the glycidyl group and the functional group of the
reacting curing agent. Usually, the ratio of the number of the
corresponding functional group of the curing agent to the number of the
glycidyl group is 0.5 to 1.5, preferably 0.7 to 1.3. By setting the ratio
of the resin component and the curing agent in the above-mentioned range,
the curing rate of the composition is not slowed, the glass transition
temperature of the cured resin is not lowered, and further the moisture
resistance is not decreased, therefore the range is suitable.

[0087]In the present invention, by reacting the admantane derivative of
the present invention, which is excellent in heat resistance and
transparency, with the above-mentioned curing agent, not only the heat
resistance and transparency but also the light resistance, and further
dielectric constant and the like are improved. In addition, solubility
which is required practically is imparted.

[0088]Furthermore, to the resin composition (1) of the present invention,
various known additives which are conventionally used, such as a curing
accelerator, an anti-deterioration agent, a modifying agent, a silane
coupling agent, a defoaming agent, inorganic powders, a solvent, a
leveling agent, a mold release agent, dye, pigment and the like may be
appropriately blended as needed.

[0089]The above-mentioned curing accelerator is not particularly limited.
The examples include 1,8-diaza-bicyclo[5.4.0]undecene-7,
triethylenediamine, tertiary amines such as
tris(2,4,6-dimethylaminomethyl)phenol and the like; imidazoles such as
2-ethyl-4-methylimidazole, 2-methylimidazole and the like; phosphorus
compounds such as triphenylphosphine, tetraphenylphophonium bromide,
tetraphenylphosphonium tetraphenylborate,
tetra-n-butylphosphonium-O,O-diethylphosphorodithioate and the like;
quarternary ammonium salts; organic metal salts; derivatives of them; and
others. These curing accelerators may be used alone or in combination.
Among these curing accelerators, it is preferable to use tertiary amines,
imidazoles, and phosphorus compounds.

[0090]The content of the curing accelerator is preferably 0.01 to 8.0
parts by mass, more preferably 0.1 to 3.0 parts by mass, relative to 100
parts by mass of the above-mentioned resin component. By setting the
content of the curing accelerator in the above-mentioned range,
sufficient curing acceleration effect is attained and there is no
discoloration in the cured product obtained.

[0091]Examples of the anti-deterioration agent include conventionally
known anti-deterioration agents such as phenolic compounds, amine
compounds, organic sulfur compounds, phosphorus compounds and the like.
By adding the anti-deterioration agent, characteristics of the resin
composition (1) of the present invention such as heat resistance,
transparency and the like are retained.

[0095]As a modifying agent, conventional known modifying agents such as
glycols, silicones, alcohols and the like may be mentioned. As a silane
coupling agent, conventional known silane coupling agents such as
silanes, titanates and the like may be mentioned. As a defoaming agent,
conventional known defoaming agents such as silicones and the like may be
mentioned. As inorganic powders, the ones having a particle diameter of
several nm to 10 μm may be used depending on the intended use. The
examples include known inorganic powders such as glass powders, silica
powders, titania, zinc oxide, alumina and the like. As a solvent, an
aromatic solvent such as toluene, xylene and the like and a ketone
solvent such as methyl ethyl ketone, methyl isobutyl ketone,
cyclohexanone and the like may be used as a diluent for a powdery resin
component or a coating agent.

[0096]As a curing method of the resin composition (1) of the present
invention, for example, a method of mixing the above-mentioned resin
component and the epoxy resin curing agent with various additives,
configuring into a desired shape by injecting the mixture into a molding
die (resin die) or by coating, and curing by heating or the ultraviolet
irradiation may be used. In the case of heat curing, the curing
temperature is usually approximately 50 to 200° C., preferably 100
to 180° C. By setting the curing temperature at 50° C. or
higher, incomplete curing is avoided. By setting the curing temperature
at 200° C. or lower, discoloration is avoided. Although the curing
time varies depending on the resin component, curing agent, accelerator,
and initiator to be used, it is preferably 0.5 to 6 hours.

[0097]Irradiation intensity of the ultraviolet light is usually
approximately 500 to 5,000 mJ/cm2, preferably 1,000 to 4,000
mJ/cm2. Post-heating may be carried out after the ultraviolet
irradiation, preferably at 70 to 200° C. for 0.5 to 12 hours.

[0098]The molding method is not particularly limited and injection
molding, blow molding, press molding and the like may be used, and the
cured product is preferably produced by injection-molding the composition
in a pellet form using an injection molding machine.

[0099]The cured product obtained by curing the resin composition (1) of
the present invention is excellent in heat resistance and transparency,
and may attain the total light transmittance as high as 70% or more. As
shown in Examples later, the cured product that is excellent in
workability because of its low dissolution temperature, has a high glass
transition temperature, excellent durability (heat resistance and light
resistance), and is excellent in electric characteristics such as
dielectric constant and the like is obtained.

[0100]Thus, since the resin composition (1) of the present invention has
excellent characteristics, it may be suitably used for an optoelectronic
part such as a resin (sealant and adhesive) for an optical semiconductor
(LED and the like), a flat panel display (organic EL element and the
like), an electronic circuit, and an optical circuit (optical waveguide),
a lens for optical communication, an optical film, and the like.

[0101]Therefore, the resin composition (1) of the present invention is
used as a semiconductor element and/or an integrated circuit (IC and the
like) and individual semiconductors (diode, transistor, thermistor, and
the like), for LED (an LED lamp, chip LED, a light receiving element, and
a lens for an optical semiconductor), a sensor (a temperature sensor, an
optical sensor, and a magnetic sensor), a passive part (a high frequency
device, a resistor, a condenser and the like), an electromechanical part
(a connector, a switch, a relay and the like), an automobile part (a
circuit system, a control system, sensors, a lamp seal and the like), and
an adhesive (optical parts, an optical disc, and a pickup lens), and
others, as well as for an optical film as a surface coating agent, and
the like.

[0102]The composition as a sealant for an optical semiconductor (LED and
the like) may be applied to an element such as bombshell type LED,
surface mount type (SMT) LED or the like. The composition satisfactorily
adheres to a semiconductor made of GaN and the like formed on a metal or
polyamide. The composition may also be used with a fluorescent dye such
as YAG and the like dispersed. Furthermore, the composition is applicable
as a surface coating agent for bombshell type LED, a lens for SMT type
LED and the like.

[0103]When applied to the organic EL, the composition is applicable to an
organic EL element having layers of a positive electrode, a
hole-injecting layer, a luminescent layer, an electron-injecting layer,
and a negative electrode in this order on a light-transmitting substrate
such as commonly-used glass, transparent resin and the like. As for a
sealant of an organic EL element, it may directly seal the EL element by
using the composition as an adhesive to cover the EL element with a metal
can, a metal foil, or a resin film coated with SiN and the like.
Alternatively, the EL element may be directly sealed by the glycidyloxy
group-containing adamantane derivative of the present invention with an
inorganic filler and the like dispersed in order to impart the gas
barrier property to the glycidyloxy group-containing adamantane
derivative. As for the display method, although the composition is
applicable to the bottom emission system which is currently mainstream,
the effect of the transparency and heat resistance of the glycidyloxy
group-containing adamantane derivative of the present invention may be
utilized by applying the composition to the top emission system which is
prospective in light extraction efficiency and the like in the future.

[0104]When applied to the electronic circuit, the resin composition is
applicable as an interlayer insulation film, an adhesive between the
polyimide for the flexible print board and copper foil, or a resin for a
substrate board.

[0105]When applied to the optical circuit, the resin composition is also
applicable to a thermooptical switch for single and multi modes, an
arrayed waveguide grating, a multi/demultiplexer, a wavelength variable
filter, or a core or clad material of optical fiber. In addition, the
resin composition is also applicable to a microlens array to condense
light to the waveguide and a mirror of MEMS type optical switch.
Furthermore, the resin composition is also applicable to a dye binder of
a photoelectric conversion element.

[0106]When used as the optical film, the resin composition is applicable
to display such as a film board for liquid crystal, a film board for
organic EL, and the like, as well as a light diffusion film, an
antireflection film, a color conversion film with a fluorescent dye and
the like dispersed, and others.

[0107]The resin composition (2) of the present invention contains the
adamantyl group-containing epoxy modified (meth)acrylate represented by
the above-mentioned general formula (III) and a thermopolymerization
initiator or a photopolymerization initiator. In the resin composition
(2) of the present invention, a mixed resin of the above-mentioned
adamantyl group-containing epoxy modified acrylates and another
polymerizable monomer may be used as long as it does not adversely affect
the transparency, heat resistance, and the like. Examples of other
polymerizable monomer include methyl (meth)acrylate, ethyl
(meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl
(meth)acrylate, dicyclopentanyl (meth)acrylate, 1-adamantyl
(meth)acrylate, ethyleneglycol di(meth)acrylate, 1,3-propanediol
di(meth)acrylate, 1,4-butanediol di(meth)acrylate, pentaerythritol
tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol
penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate,
trimethylolpropane tri(meth)acrylate, ditrimethylolpropane
tetra(meth)acrylate, adamantanediol di(meth)acrylate,
adamantanedimethanol di(meth)acrylate, adamantanediethanol
di(meth)acrylate and the like. These monomers may be used alone or in
combination of two or more kinds.

[0108]In addition, in the resin composition (2) of the present invention,
a mixture of the adamantyl group-containing epoxy modified acrylates
represented by the above-mentioned general formula (III) and an epoxy
(meth)acrylate obtained by a reaction of the known epoxy resin
exemplified in the above-mentioned resin composition (1) and
(meth)acrylic acid may be used.

[0109]In the mixed resin of the adamantyl group-containing epoxy modified
acrylates represented by the above-mentioned general formula (III) and
the above-mentioned other polymerizable monomer and/or epoxy resin
modified (meth)acrylate, the content of the above-mentioned adamantyl
group-containing epoxy modified acrylates is preferably 5 mass % or more,
more preferably 10 mass % or more. When the content of the adamantyl
group-containing epoxy modified acrylates is 5 mass % or more, the
optical characteristics, long term heat resistance, and electric
characteristics of the resin composition (2) of the present invention are
sufficient.

[0110]The resin composition (2) of the present invention is cured by
polymerization using a thermopolymerization initiator or a
photopolymerization initiator. As the thermopolymerization initiator, one
which reacts with a group having an unsaturated bond, that is, an
acryloyl group or a methacryloyl group by heat may be used. The examples
include an organic peroxide such as benzoyl peroxide, methyl ethyl ketone
peroxide, methyl isobutyl ketone peroxide, cumene hydroperoxide, t-butyl
hydroperoxide and the like, an azo initiator such as
azobisisobutyronitrile and the like, and others. These initiators may be
used alone or in combination of two or more kinds.

[0111]As the photopolymerization initiator, one which reacts with a group
having an unsaturated bond, that is, an acryloyl group or a mathacryloyl
group by light irradiation may be used. The examples include
acetophenones, benzophenones, benzils, benzoin ethers, benzil diketals,
thioxanthones, acylphosphine oxides, acylphosphinic acid esters, aromatic
diazonium salts, aromatic sulfonium salts, aromatic iodonium salts,
aromatic iodosyl salts, aromatic sulfoxonium salts, metallocene
compounds, and the like. These initiators may be used alone or in
combination of two or more kinds.

[0112]The amount of the thermopolymerization initiator or
photopolymerization initiator to be used is preferably 0.01 to 10 parts
by mass, more preferably 0.05 to 5 parts by mass, relative to 100 parts
by mass of the above-mentioned adamantyl group-containing epoxy modified
acrylates or the above-mentioned mixed resin (hereinafter, sometimes
referred to as "resin component"). By setting the content of the
polymerization initiator in the above-mentioned range, good
polymerization characteristics and physical properties such as optical
characteristics and the like are expressed.

[0113]The resin composition (2) of the present invention may be added with
various known additives which are conventionally used, such as an
anti-deterioration agent, a modifying agent, a silane coupling agent, a
defoaming agent, inorganic powder, a solvent, a leveling agent, a mold
release agent, dye, pigment and the like, as needed. Specific examples of
the anti-deterioration agent and the like are similar to those
exemplified in the above-mentioned resin composition (1).

[0114]The resin composition (2) of the present invention is photocured by
mixing the above-mentioned resin component, a thermopolymerization
initiator or a photopolymerization initiator, and various additives,
configuring into a desired shape by injecting the mixture into a molding
die (resin die) or by coating, and heating or irradiating with an
ultraviolet light and the like. In the case of heat curing, the curing
temperature is usually approximately 30 to 200° C., preferably 50
to 150° C. By setting the curing temperature at 30° C. or
higher, incomplete curing is avoided. By setting the curing temperature
at 200° C. or lower, discoloration and the like are avoided.
Although the curing time varies depending on the resin component,
polymerization initiator and the like to be used, it is preferably 0.5 to
6 hours.

[0115]In the case of photocuring by the ultraviolet irradiation, although
the irradiation intensity of the ultraviolet light is optionally
determined by the kind of the resin component and the polymerization
initiator, film thickness of the cured product, and the like, it is
usually approximately 100 to 5,000 mJ/cm2, preferably 500 to 4,000
mJ/cm2. Post-heating may be carried out after the ultraviolet
irradiation, preferably at 70 to 200° C. for 0.5 to 12 hours.

[0116]The molding method is not particularly limited and injection
molding, blow molding, press molding and the like may be used, and the
cured product is preferably produced by injection-molding the resin
composition in a pellet form using an injection molding machine.

[0117]The cured product obtained by curing the resin composition (2) of
the present invention is excellent in transparency, heat resistance, and
mechanical properties such as hardness and the like, and may be
advantageously used as a solder resist for an interconnection substrate,
a protection film for a color filter of a liquid crystal display and an
image sensor, a colored composition for a color filter, a sealant for an
electronic circuit (a sealant for an optical semiconductor and a sealant
for an organic EL element), an optoelectronic part (an optical waveguide,
a lens for optical communication, an optical film, and the like), and
adhesives for these devices, and others.

[0118]Furthermore, the resin composition (2) of the present invention is
used as a semiconductor element and/or an integrated circuit (IC and the
like) and individual semiconductors (diode, transistor, thermistor, and
the like), for LED (an LED lamp, chip LED, a light receiving element, and
a lens for an optical semiconductor), a sensor (a temperature sensor, an
optical sensor, and a magnetic sensor), a passive part (such as a high
frequency device, a resistor, a condenser and the like), an
electromechanical part (such as a connector, a switch, a relay and the
like), an automobile part (such as a circuit system, a control system,
sensors, a lamp seal and the like), an adhesive (an optical part, an
optical disc, and a pickup lens), and others, as well as for an optical
film and the like as a surface coating agent.

EXAMPLES

[0119]Hereinafter the present invention is explained in more detail by
Examples. The present invention is not at all limited by these Examples.
In the following Examples and Comparative Examples, the obtained
composition and the like were evaluated as follows.

(1) Glass Transition Temperature

[0120]Glass transition temperature was defined as a discontinuous point
observed on a heat flux curve obtained by raising the temperature of 10
mg of a sample at a rate of 10° C./min after keeping the sample at
50° C. for 5 minutes under nitrogen atmosphere, using a
differential scanning calorimeter (DSC-7 manufactured by PerkinElmer
Inc.).

(2) Light Transmittance

[0121]Light transmittance was measured according to JIS K7105 using a
sample piece of 3 mm thick at a measurement wavelength of 400 nm (unit:
%). A spectrophotometer UV-3100S manufactured by Shimadzu Corporation was
used as the measurement apparatus.

(3) Light Resistance Test

[0122]The sample was irradiated with a light at 60° C. for 500
hours using SUNTEST CPS+ manufactured by Toyo Seiki Seisaku-sho, Ltd. and
the change of the light transmittance at 400 nm before and after the
irradiation was measured using a sunshine tester. When the rate of
decrease of the light transmittance is less than 20%, the evaluation is
"good". When the rate of decrease is 20% or more, the evaluation is
"poor".

(4) Long Term Heat Resistance Test

[0123]The sample was placed in a constant temperature bath at 140°
C. for 100 hours and the change of the light transmittance at 400 nm
before and after the testing was measured using a sunshine tester. When
the light transmittance decreased 20% or more, the evaluation is "poor".

EXAMPLE 1

Synthesis of 4,6-bis(1-adamantyl)-1,3-dihydroxybenzene

[0124]A 500 mL four-necked flask equipped with a reflux condenser, a
stirrer, a thermometer, and a nitrogen inlet tube was charged with 28.1 g
(0.18 mol) of 1-adamantanol, 15.84 g (0.09 mol) of p-toluenesulfonic acid
monohydrate, and 300 mL of heptane and replaced with nitrogen. The
mixture was added with 9.9 g (0.09 mol) of resorcinol. The flask was
immersed in an oil bath at 100° C. and the mixture was heated
while stirring for 1 hour. After cooling the reaction mixture, the solid
content was collected by filtration, which was then dried under vacuum,
followed by recrystallization by aqueous methanol solution to obtain
4,6-bis(1-adamantyl)-1,3-dihydroxybenzene (yield: 86%, LC (liquid
chromatography) purity: 99.7%, melting point: 146° C.). Note that
the LC purity was measured by absorbance at λ=280 nm.

[0125]The obtained 4,6-bis(1-adamantyl)-1,3-dihydroxybenzene, was
identified by nuclear magnetic resonance spectrum (1H--NMR and
13C--NMR). The spectrum data are shown below. The nuclear magnetic
resonance spectrum was measured using chloroform-d as a solvent and
JNM-ECA500 manufactured by JEOL Ltd. as a measurement apparatus.

[0128]A 500 mL four-necked flask equipped with a reflux condenser, a
stirrer, a thermometer, and a nitrogen inlet tube was charged with 57 mL
of MIBK, 157 mL of DMSO, and 98 g (1.057 mol) of epichlorohydrin and
replaced with nitrogen for 30 minutes. To this solution, 52.01 g (0.137
mol) of 4,6-bis(1-adamantyl)-1,3-dihydroxybenzene synthesized in Example
1 was added, and the flask was replaced with nitrogen for 30 minutes and
then heated at 45° C. while stirring. This solution was added with
11.6 g (0.290 mol) of sodium hydroxide over 0.5 hour and the solution was
stirred for 1.5 hours. Then, 2.9 g (0.0725 mol) of sodium hydroxide was
added and the solution was further stirred for 1 hour. The reaction
mixture was cooled to room temperature, and 300 mL of chloroform was
added. After washing with 500 mL of water, an aqueous 0.1 mol/L HCl
solution was added to the mixture and the organic layer was separated.
After further washing with water until the aqueous phase became neutral,
the organic layer was concentrated and dried until the weight became
constant in a reduced pressure drier at 100° C. to obtain
4,6-bis(1-adamantyl)-1,3-diglycidyloxybenzene as a pale-yellow solid
(yield: 92%, LC purity: 99.20%, epoxy equivalent: 267, melting point:
193° C.).

[0129]The obtained 4,6-bis(1-adamantyl)-1,3-diglycidyloxybenzene, was
identified by nuclear magnetic resonance spectrum (1H--NMR and
13C--NMR). The spectrum data are shown below. The nuclear magnetic
resonance spectrum was measured using chloroform-d as a solvent and
JNM-ECA500 manufactured by JEOL Ltd. as a measurement apparatus.

[0132]5 g of 4,6-bis(1-adamantyl)-1,3-diglycidyloxybenzene obtained in
Example 2, 3.06 g of methylhexahydrophthalic anhydride (MH700
manufactured by New Japan Chemical Co., Ltd.) as an acid anhydride, and
0.1 g of octylic acid salt of 1,8-diazabicyclo[5.4.0]undecene-7 (SA102
manufactured by San-Apro Ltd.) as a curing accelerator were mixed at room
temperature and, after defoaming, the mixture was heated at 110°
C. for 2 hours and then at 170° C. for 4 hours to produce the
cured resin (a sheet of 3 mm thickness). The glass transition temperature
and light transmittance of the obtained cured resin product were
measured, and further the light resistance test and long term heat
resistance test were carried out. The evaluation results are shown in
Table 1.

EXAMPLE 4

[0133]2.5 g of 4,6-bis(1-adamantyl)-1,3-diglycidyloxybenzene obtained in
Example 2, 2.5 g of bisphenol-A type epoxy resin (Epikote 828
manufactured by Japan Epoxy Resins Co., Ltd.), 3.73 g of
methylhexahydrophthalic anhydride (MH700 manufactured by New Japan
Chemical Co., Ltd.) as an acid anhydride, and 0.1 g of octylic acid salt
of 1,8-diazabicyclo[5.4.0]undecene-7 (SA102 manufactured by San-Apro
Ltd.) as a curing accelerator were mixed at room temperature and, after
defoaming, the mixture was heated at 110° C. for 2 hours and then
at 170° C. for 4 hours to produce the cured resin (a sheet of 3 mm
thickness). The obtained cured resin product was evaluated similarly to
those in Example 1. The evaluation results are shown in Table 1.

Comparative Example 1

[0134]Except for bisphenol-A type epoxy resin (Epikote 828 manufactured by
Japan Epoxy Resins Co., Ltd.) was used instead of
4,6-bis(1-adamantyl)-1,3-diglycidyloxybenzene in Example 3 and 4.40 g of
methylhexahydrophthalic anhydride was used, the cured resin was produced
by a similar method to that in Example 1 and evaluated similarly. The
evaluation results are shown in Table 1.

[0135]A 300 mL separable flask equipped with a reflux condenser, a
stirrer, a thermometer, and an air inlet tube was charged with 18.8 g of
4,6-bis(1-adamantyl)-1,3-diglycidyloxybenzene obtained in Example 2, 6.1
g of acrylic acid, 50 mL of toluene, 0.61 g of tetraethylammonium
bromide, and 6.1 mg of p-methoxyphenol. The mixture was heated to
120° C. under an air stream of a low flow rate and stirred for 20
hours. Then, 80 mL of toluene was added to the reaction mixture, which
was cooled to room temperature. The toluene solution was washed twice
with aqueous 5 mass % sodium chloride solution and once with pure water,
followed by concentrating the organic layer to obtain 23.2 g of adamantyl
group-containing epoxy modified acrylate represented by the following
formula (LC purity: 91%).

##STR00010##

[0136]The adamantyl group-containing epoxy modified acrylate was
identified by nuclear magnetic resonance spectrum (1H--NMR and
13C--NMR). The spectrum data are shown below. The nuclear magnetic
resonance spectrum was measured using chloroform-d as a solvent and
JNM-ECA500 manufactured by JEOL Ltd. as a measurement apparatus.

[0139]10 g of epoxy modified acrylate obtained in Example 5 and 0.1 g of
benzoin isobutyl ether as a photopolymerization initiator was mixed to
prepare a resin composition, the obtained resin composition was applied
on a glass substrate so that the applied thickness is 0.1 mm and
irradiated with a high pressure mercury lamp to cure. The glass
transition temperature of the obtained cured product was as high as
184° C.

INDUSTRIAL APPLICABILITY

[0140]The adamantane derivative of the present invention provides a cured
product excellent in optical characteristics such as transparency, (long
term) light resistance and the like, (long term) heat resistance, and
mechanical properties, and is suitable as a solder resist for an
interconnection substrate, a protection film for a color filter of a
liquid crystal display and an image sensor, a colored composition for a
color filter, a sealant for an electronic circuit (a sealant for an
optical semiconductor and a sealant for an organic EL element), an
optoelectronic part (an optical waveguide, a lens for optical
communication, an optical film, and the like), adhesives for these
devices, and others.